1,1'-Carbonyldiimidazole → HCID 57619816, compound

HRID 1642473Notes

Reaction equation

HRID 1642473 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2([CH3:28])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:11][CH2:10]1.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30]>C(#N)C>[O:30]=[C:29]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]3([CH3:28])[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]3)[CH2:11][CH2:10]2)[C@H:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]2[NH:1]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57619826HCID 57619826, compound

Product 1

HCID 57619816HCID 57619816, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of tert-butyl 4-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-4-methyl-piperidine-1-carboxylate (10.0 mmol) in acetonitrile (30 mL) was added with 1,1′-carbonyldiimidazole (1.95 g, 12.0 mmol) and stirred at room temperature for 12 h. Concentrated in vacuo and was added with water (20 mL) and dichloromethane (100 mL), phases were separated and the aqueous phase was extracted with dichloromethane (2×50 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with preparative LC/MS (high pH) to provide the title compound as white solid (1.18 g, 28% over two steps). 1H NMR (400 MHz, METHANOL-D4) δ ppm 0.95 (s, 3H), 1.31-1.40 (m, 4H), 1.42 (s, 9H), 1.44-1.48 (m, 2H), 1.52-1.63 (m, 1H), 1.64-1.89 (m, 8H), 1.93-1.99 (m, 1H), 2.08-2.21 (m, 2H), 2.25-2.32 (m, 1H), 2.89-3.10 (m, 4H), 3.28-3.36 (m, 1H), 3.42-3.53 (m, 2H), 3.54-3.65 (m, 1H). MS (M+1): 421.3.

Workup

  1. concentrationConcentrated in vacuo
  2. additionwas added with water (20 mL) and dichloromethane (100 mL), phases
  3. customwere separated
  4. extractionthe aqueous phase was extracted with dichloromethane (2×50 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified with preparative LC/MS (high pH)

Sources & evidence

ORD record
ord-60423dbc2fbb438aacd5f5b058103694
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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